Chemistry Reference
In-Depth Information
Styramate [94-35-9], muscle relaxant, antispasmodic, 215.
1-Phenyl-1,2-ethanediol-2-
carbamate 215 is obtained by phosgenation of the corresponding diol 214 [156].
OH
OH
OH
1.
COCl
2
O
NH
2
2. NH
3
O
214
215
Styramate
Sulfaperin [599-88-2], chemotherapeutic, 220.
Phosgene is reacted with N,N-dime-
thylformamide to give intermediate 216, which is then treated with 1-ethoxy-1-
propene to form a C-4 synthon. Reaction of the latter with the sulfaguanidine 219
forms the 1,3-diazine Sulfaperin 220 [157].
_
O
O
Cl
217
COCl
2
Cl
O
N
O
Cl
NCHO
O
N
O
216
218
H
NNH
2
NH
O
S
O
H
2
N
219
H
N
O
N
S
O
N
H
2
N
220
Sulfaperin
A similar method has been applied in the synthesis of Trimethoprim [738-70-5], a
chemotherapeutic, antibacterial API (reaction of 3,4,5-trimethoxybenzylcyanoacetic
acid with DMF and phosgene, followed by reaction with guanidine, leads directly to
trimethoprim) [158, 159].
Temocillin [66148-78-5], b-lactam antibiotic (penicillin derivative), 224. In one method,
phosgene is employed to generate the isonitrile function of the penicillanic acid
ester 223 [160-162].
